EA029901B1 - Соединения для применения в качестве иммуномодуляторов - Google Patents
Соединения для применения в качестве иммуномодуляторов Download PDFInfo
- Publication number
- EA029901B1 EA029901B1 EA201690316A EA201690316A EA029901B1 EA 029901 B1 EA029901 B1 EA 029901B1 EA 201690316 A EA201690316 A EA 201690316A EA 201690316 A EA201690316 A EA 201690316A EA 029901 B1 EA029901 B1 EA 029901B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methyl
- methoxy
- phenyl
- phenylphenyl
- amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 344
- 239000002955 immunomodulating agent Substances 0.000 title abstract 2
- 229940121354 immunomodulator Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 76
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 74
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 201000011510 cancer Diseases 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 208000035475 disorder Diseases 0.000 claims abstract description 8
- -1 hydroxycyclopentyl Chemical group 0.000 claims description 342
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 210
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 177
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 176
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 142
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 97
- 150000003839 salts Chemical class 0.000 claims description 85
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 40
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 38
- 150000001412 amines Chemical class 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 33
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 33
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 30
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 25
- 235000019260 propionic acid Nutrition 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 239000003937 drug carrier Substances 0.000 claims description 11
- 230000003993 interaction Effects 0.000 claims description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 9
- RUJGJXQLELAMPZ-UHFFFAOYSA-N Cc1cc(CN2CCC2)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCC2)ccc1OCc1cccc(c1C)-c1ccccc1 RUJGJXQLELAMPZ-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 8
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
- YCCDVBIIHLIURK-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)(C)CN1CCN(C)CC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)(C)CN1CCN(C)CC1 YCCDVBIIHLIURK-UHFFFAOYSA-N 0.000 claims description 7
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- MVXPOSMNRSCJMP-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CC(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CC(O)=O MVXPOSMNRSCJMP-UHFFFAOYSA-N 0.000 claims description 6
- GNYIPNWZSMMUFQ-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCC3)cc2)cccc1-c1ccccc1F Chemical compound Cc1c(COc2ccc(CN3CCC3)cc2)cccc1-c1ccccc1F GNYIPNWZSMMUFQ-UHFFFAOYSA-N 0.000 claims description 6
- RVDAEQRWSPNFRG-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCOCC3C(O)=O)cc2Cl)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCOCC3C(O)=O)cc2Cl)cccc1-c1ccccc1 RVDAEQRWSPNFRG-UHFFFAOYSA-N 0.000 claims description 6
- NUYRSTFEAVNXBY-UHFFFAOYSA-N Cc1c(COc2ccc3CNCCc3c2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc3CNCCc3c2)cccc1-c1ccccc1 NUYRSTFEAVNXBY-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- KFGVVLYYXUEFDP-UHFFFAOYSA-N 2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]-1-morpholin-4-ylethanone Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(=O)N1CCOCC1 KFGVVLYYXUEFDP-UHFFFAOYSA-N 0.000 claims description 5
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 5
- YVZRCGTUVFCWHV-UHFFFAOYSA-N CC1=C(COC2=CC=C(CNCCO)C=C2Cl)C=CC=C1C1=CC=CC=C1 Chemical compound CC1=C(COC2=CC=C(CNCCO)C=C2Cl)C=CC=C1C1=CC=CC=C1 YVZRCGTUVFCWHV-UHFFFAOYSA-N 0.000 claims description 5
- NGWARGISBMFXGR-UHFFFAOYSA-N CN(CC(O)=O)Cc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1 Chemical compound CN(CC(O)=O)Cc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1 NGWARGISBMFXGR-UHFFFAOYSA-N 0.000 claims description 5
- GKSRPCFFAXGNIE-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCCN1CCCC1=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCCN1CCCC1=O GKSRPCFFAXGNIE-UHFFFAOYSA-N 0.000 claims description 5
- RWOWRLYCKOPZHJ-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCO RWOWRLYCKOPZHJ-UHFFFAOYSA-N 0.000 claims description 5
- IDRDYZSWSKCIGO-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN1CCC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN1CCC1 IDRDYZSWSKCIGO-UHFFFAOYSA-N 0.000 claims description 5
- OBTLAGVBBUQHSK-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCC3)cc2Cl)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCC3)cc2Cl)cccc1-c1ccccc1 OBTLAGVBBUQHSK-UHFFFAOYSA-N 0.000 claims description 5
- OAHMJAXIBOFXIV-UHFFFAOYSA-N Cc1cc(OCc2cccc(c2C)-c2ccccc2)cc(C)c1CN1CCCCC1C(O)=O Chemical compound Cc1cc(OCc2cccc(c2C)-c2ccccc2)cc(C)c1CN1CCCCC1C(O)=O OAHMJAXIBOFXIV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- IVIKGKAWCGPRBQ-UHFFFAOYSA-N 2-methylhept-6-enoic acid Chemical class OC(=O)C(C)CCCC=C IVIKGKAWCGPRBQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
- VRIBDHIYQYBONN-UHFFFAOYSA-N CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Br)c1 Chemical compound CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Br)c1 VRIBDHIYQYBONN-UHFFFAOYSA-N 0.000 claims description 4
- RSILUGRGGAUUNL-UHFFFAOYSA-N CC=1C=C(C=CC=1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CN1CC(=CCC1)C(=O)O Chemical compound CC=1C=C(C=CC=1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CN1CC(=CCC1)C(=O)O RSILUGRGGAUUNL-UHFFFAOYSA-N 0.000 claims description 4
- UQQACMJMIXWAQX-UHFFFAOYSA-N CN(CC(O)=O)Cc1cccc(OCc2cccc(c2C)-c2ccccc2)c1 Chemical compound CN(CC(O)=O)Cc1cccc(OCc2cccc(c2C)-c2ccccc2)c1 UQQACMJMIXWAQX-UHFFFAOYSA-N 0.000 claims description 4
- MVYOGUBAUCKKAM-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN1CCC1 Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN1CCC1 MVYOGUBAUCKKAM-UHFFFAOYSA-N 0.000 claims description 4
- ZBOYJODMIAUJHH-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN1CCCCC1C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN1CCCCC1C(O)=O ZBOYJODMIAUJHH-UHFFFAOYSA-N 0.000 claims description 4
- DJTHSGNSQOGZGD-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)CC(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)CC(O)=O DJTHSGNSQOGZGD-UHFFFAOYSA-N 0.000 claims description 4
- BLOGSJFQUAQIQG-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCC(N)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCC(N)=O BLOGSJFQUAQIQG-UHFFFAOYSA-N 0.000 claims description 4
- MFEHNRXGUMAKJB-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCC1=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCC1=O MFEHNRXGUMAKJB-UHFFFAOYSA-N 0.000 claims description 4
- YZASPJDRTJDVGZ-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCCC1=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCCC1=O YZASPJDRTJDVGZ-UHFFFAOYSA-N 0.000 claims description 4
- MDRNRIAYLGGFKE-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCNC(=O)C1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCNC(=O)C1 MDRNRIAYLGGFKE-UHFFFAOYSA-N 0.000 claims description 4
- KQDCXYBUWMBUSN-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCC(CC3)C(O)=O)cc2Cl)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCC(CC3)C(O)=O)cc2Cl)cccc1-c1ccccc1 KQDCXYBUWMBUSN-UHFFFAOYSA-N 0.000 claims description 4
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- QRXBPPWUGITQLE-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cc2Br)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cc2Br)cccc1-c1ccccc1 QRXBPPWUGITQLE-UHFFFAOYSA-N 0.000 claims description 4
- XQIVBIQDGUDOIA-UHFFFAOYSA-N Cc1c(COc2cccc(CN3CCC3)c2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2cccc(CN3CCC3)c2)cccc1-c1ccccc1 XQIVBIQDGUDOIA-UHFFFAOYSA-N 0.000 claims description 4
- BQUUEFHIMNASHV-UHFFFAOYSA-N Cc1c(COc2cccc(CNCCCN3CCCC3=O)c2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2cccc(CNCCCN3CCCC3=O)c2)cccc1-c1ccccc1 BQUUEFHIMNASHV-UHFFFAOYSA-N 0.000 claims description 4
- YSKRXTFVLTYIRJ-UHFFFAOYSA-N Cc1cc(CN2CCCCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCCCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 YSKRXTFVLTYIRJ-UHFFFAOYSA-N 0.000 claims description 4
- UAKMDFGBYWWAOW-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCN1CCN(C)CC1 UAKMDFGBYWWAOW-UHFFFAOYSA-N 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 4
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 4
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229960004063 propylene glycol Drugs 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- ZHJPFAIDYVOVEG-UHFFFAOYSA-N 1-[3-[[3-methyl-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]propyl]pyrrolidin-2-one Chemical compound CC=1C=C(C=CC=1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CNCCCN1C(CCC1)=O ZHJPFAIDYVOVEG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- IADUEWIQBXOCDZ-VKHMYHEASA-N Azetidine-2-carboxylic acid Natural products OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 claims description 3
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- C07C2601/14—The ring being saturated
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- C—CHEMISTRY; METALLURGY
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- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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2014
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- 2014-09-02 BR BR112016004194A patent/BR112016004194A8/pt not_active Application Discontinuation
- 2014-09-02 CA CA2923184A patent/CA2923184A1/fr not_active Abandoned
- 2014-09-02 MX MX2016002544A patent/MX2016002544A/es unknown
- 2014-09-02 ES ES14766086.4T patent/ES2642074T3/es active Active
- 2014-09-02 US US14/915,782 patent/US9872852B2/en active Active
- 2014-09-02 PE PE2016000338A patent/PE20160432A1/es not_active Application Discontinuation
- 2014-09-02 SG SG11201601225RA patent/SG11201601225RA/en unknown
- 2014-09-02 WO PCT/US2014/053695 patent/WO2015034820A1/fr active Application Filing
- 2014-09-02 EA EA201690316A patent/EA029901B1/ru not_active IP Right Cessation
- 2014-09-02 EP EP14766086.4A patent/EP3041822B1/fr active Active
- 2014-09-02 CN CN201480060895.6A patent/CN105705489B/zh active Active
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2016
- 2016-02-29 IL IL24434616A patent/IL244346B/en not_active IP Right Cessation
- 2016-03-04 CL CL2016000508A patent/CL2016000508A1/es unknown
- 2016-10-06 HK HK16111624.3A patent/HK1223366A1/zh not_active IP Right Cessation
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2018
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Patent Citations (1)
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WO1999017777A1 (fr) * | 1997-10-08 | 1999-04-15 | Merck & Co., Inc. | Inhibiteurs de transferase de prenyl-proteine |
Non-Patent Citations (1)
Title |
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DONGSHENG HUANG: "Synthetic small peptides acting on B7H1 enhance apoptosis in pancreatic cancer cells", MOLECULAR MEDICINE REPORTS, D. A. SPANDIDOS, 27 June 2012 (2012-06-27), XP055133284, ISSN: 17912997, DOI: 10.3892/mmr.2012.970 * |
Also Published As
Publication number | Publication date |
---|---|
PE20160432A1 (es) | 2016-05-11 |
HK1223366A1 (zh) | 2017-07-28 |
KR20160048946A (ko) | 2016-05-04 |
IL244346B (en) | 2019-10-31 |
BR112016004194A8 (pt) | 2020-02-11 |
AU2014315457B2 (en) | 2018-05-10 |
CA2923184A1 (fr) | 2015-03-12 |
CN105705489A (zh) | 2016-06-22 |
ES2642074T3 (es) | 2017-11-15 |
US9872852B2 (en) | 2018-01-23 |
CL2016000508A1 (es) | 2016-11-04 |
US20160194307A1 (en) | 2016-07-07 |
CL2018000150A1 (es) | 2018-05-11 |
EP3041822B1 (fr) | 2017-08-09 |
MX2016002544A (es) | 2016-06-17 |
JP2016536333A (ja) | 2016-11-24 |
CN105705489B (zh) | 2019-04-26 |
EA201690316A1 (ru) | 2016-07-29 |
IL244346A0 (en) | 2016-04-21 |
SG11201601225RA (en) | 2016-03-30 |
KR102276644B1 (ko) | 2021-07-13 |
EP3041822A1 (fr) | 2016-07-13 |
JP6417419B2 (ja) | 2018-11-07 |
WO2015034820A1 (fr) | 2015-03-12 |
AU2014315457A1 (en) | 2016-04-28 |
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